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<p>Halogenation of 3-nitro-6-phenyl- and 3-formyl-6-phenyl-2<i>H</i>-thiopyrans with bromine or iodine nitrate led to 5-halo-2<i>H</i>-thiopyrans. Chlorination of 3-nitro-6-phenyl-2<i>H</i>-thiopyrans and imides of 6-phenyl-2<i>H</i>-thiopyran-2,3-dicarboxylic acids resulted in (2<i>R</i>*,3<i>S</i>*,4<i>R</i>*)-configured 2,3,4-trichloro-3,4-dihydro-2<i>H</i>-thiopyrans. Bromination of 3-nitro-2<i>H</i>-thiopyrans was shown to proceed under conditions of both electrophilic and radical halogenation.</p>

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Halogenation of 2H-thiopyrans containing 3-positioned electron-withdrawing substituents

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • I. D. Karpov,
  • A. V. Kolobov,
  • V. A. Tafeenko,
  • V. G. Nenajdenko,
  • A. S. Aldoshin,
  • K. L. Ovchinnikov

摘要

Halogenation of 3-nitro-6-phenyl- and 3-formyl-6-phenyl-2H-thiopyrans with bromine or iodine nitrate led to 5-halo-2H-thiopyrans. Chlorination of 3-nitro-6-phenyl-2H-thiopyrans and imides of 6-phenyl-2H-thiopyran-2,3-dicarboxylic acids resulted in (2R*,3S*,4R*)-configured 2,3,4-trichloro-3,4-dihydro-2H-thiopyrans. Bromination of 3-nitro-2H-thiopyrans was shown to proceed under conditions of both electrophilic and radical halogenation.